WWE: Ranking all 40 Hell in a Cell matches from worst to best

WWE Owner Vincent Kennedy McMahon (c) flanked by superstars The Undertaker (l) and Brock Lesnar (r) (Photo by Simon Galloway - PA Images via Getty Images)
WWE Owner Vincent Kennedy McMahon (c) flanked by superstars The Undertaker (l) and Brock Lesnar (r) (Photo by Simon Galloway - PA Images via Getty Images) /
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5. Undisputed Championship: Brock Lesnar (c) vs. The Undertaker

When and Where: No Mercy on October 20, 2002, in North Little Rock, AR

We’ve arrived at the top five, and these truly stand above the rest in their own special ways. To start things off, we have a gem from the early days of Brock Lesnar. Back in 2002, Lesnar was on a tear like few had ever seen. He tore through The Rock, Hulk Hogan, and looked here to finish off The Undertaker inside of Hell in a Cell.

Paul Heyman was right at Brock Lesnar side here, as was evidenced by the odd build to the match. Heyman had found a woman who alleged to have had an affair with The Undertaker, which is just scratching the surface on the weirdness. Skipping over that nonsense, this match really got special once the bell rang.

The Undertaker’s hand had also been injured in the lead up to this match, which is why he wore a thick cast when the match began. The cast gave The Undertaker an early edge, as he could use it as a handheld weapon, but Brock Lesnar then focused on removing the cast.

Heyman stayed involved from the outside, using his belt to trap Taker’s hand against the cell so that Lesnar could wail on it with a chair until the cast broke apart. As things continued to escalate, Lesnar finally countered a Tombstone Piledriver into an F5 which gave him the win in what remains one of my favorite Hell in a Cell matches.

4. The Undertaker vs. Mankind

When and Where: King of the Ring on June 28, 1998, in Pittsburgh, PA

I’m sure you were wondering when this one would come up. There’s just no denying what it means for Hell in a Cell history. While not the greatest ever, it was the power of a few key moments and what this match has come to represent that carry it up the list. The Undertaker and Mankind went to war early, and you might have forgotten that the iconic moment we remember most wasn’t even late in this match.

Mankind being thrown off the cell and through the table was one of the first big moments we saw, and things were just getting started. While Terry Funk came to the aid of his friend, and medical help came out, Mankind refused to let things end that easily. He fought his way back into the match, and they went on to do even more amazing spots.

The action got to the top, leading to the cringe-inducing chokeslam through the cell that came close to ending Foley’s career. There were even thumbtacks at play, as The Undertaker finally finished off a battered and broken Mankind to take the victory in one of the most memorable Hell in a Cell matches we’ve ever seen.

3. WWF Title No. 1 Contendership: The Undertaker vs. Shawn Michaels

When and Where: Badd Blood: In Your House on October 5, 1997, in St. Louis, MO

The first-ever Hell in a Cell match remains one of the absolute best. Not only did it seek to solve boiling issues between Shawn Michaels and The Undertaker, but to decide who would get the right to challenge Bret Hart for the WWF Championship at Survivor Series 1997. Some readers might have already realized, Survivor Series 1997 was home to the infamous Montreal Screwjob.

There’s a lot of history wrapped into this match, and that connection doesn’t even have anything to do with the events of the match itself. We saw lots of moments that would come to be staples of HIAC first exhibited as early as this match, whether it was crew being “injured” and causing the door to be opened, people falling off the cell through tables, steel chairs, steel stairs, it was all there.

There was even a surprise appearance, this one being the historic debut of Kane. “That’s gotta be Kane,” Vince McMahon screamed from commentary as the arena glowed red and The Undertaker’s long-lost brother appeared. He attacked Undertaker, hitting the Tombstone Piledriver on him and ultimately helping Shawn Michaels pick up the win in what still remains a truly classic and unforgettable contest.

2. The Undertaker vs. Edge

When and Where: SummerSlam on August 17, 2008, in Indianapolis, IN

Here we are. Number two. You’ve probably already glanced at number one, but stay a minute here and appreciate what carries this 2008 Hell in a Cell match so close to the top of the list. The issues between The Undertaker and Edge began nearly one year before this when Batista defended his World Heavyweight Championship inside Hell in a Cell against The Undertaker.

That match landed all the way back at 28 on this list, but it planted the seeds for one of the greatest ones we’ve ever seen. Edge revealed himself to have been in disguise as a cameraman inside the structure, as he ambushed The Undertaker and cost him the match. It began a bitter rivalry that hit an apex at WrestleMania 24 when The Undertaker captured the World Heavyweight Championship by defeating Edge in the main event.

That bitter rivalry continued to boil, arriving at the true peak at SummerSlam that same year. This was also the last Hell in a Cell match prior to the creation of the Hell in a Cell pay-per-view, which certainly feels like an “end of an era” in HIAC history. The match intensified quickly, with Edge spearing The Undertaker into the steel stairs just as this one started to get rolling.

Edge definitely went back to his TLC roots here, as tables, ladders, and chairs were all focal points throughout the contest. He used all three in a moment that was an ingenious callback to something Edge had done to Mick Foley only a few weeks prior. The match even spilled to the outside, as Edge speared Undertaker through the cell itself and a few moments later through an announce table.

Earlier in the match, Edge had set up and stacked two tables just outside the ring between the mat and the cell structure. Unfortunately, Chekhov’s tables came back to bite him as The Undertaker chokeslammed Edge off the top rope and through both tables. After taking the win, The Undertaker wasn’t done as he chokeslammed Edge all the way through the ring, even raising fire through the hole in the ring to signify the absolute end of “The Rated R Superstar.”

1. WWF Championship: Triple H (c) vs. Cactus Jack

When and Where: No Way Out on February 27, 2000, in Hartford, CT

Here we are. The cream of the crop. The absolute top. The best of the best. Number one out of all 40 Hell in a Cell matches that have ever happened. This is one where I found some agreement, as this had been ranked at the absolute top on two other lists. I vividly remembered much of this match, as I’ve seen it several times. I honestly believed this might end up being my top match after taking the time to watch it yet again for this journey, and I wasn’t surprised when the dust settled and it topped my list.

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The stakes couldn’t have been higher. Not only was the WWF Championship at stake, and the chance to walk into WrestleMania 16 as the champion, but Cactus Jack would be forced to retire if he couldn’t defeat Triple H inside Hell in a Cell. It was the first time Triple H ever entered HIAC, the same man who today has nine appearances and six victories to his name from his time inside Satan’s Structure. Only The Undertaker has more, but his winning percentage isn’t quite as high.

Once the match began, it was clear these two would be taking things to a whole new level. Barely one month after they’d bled buckets in a Street Fight for the title at Royal Rumble 2000, Cactus Jack and Triple H went to war one more time. The motivation was clearly there for Jack, or Mankind, or Mrs. Foley’s Baby Boy, or whatever you’d like to call him, as he came flying off the top turnbuckle for a steel chair assisted elbow drop to an opponent down on the outside.

Predictably, the match spilled outside of the cell and carried the action to the area where announcers flee during Hell in a Cell. Foley cranked the intensity up a notch by retrieving a 2×4 wrapped in barbed wire, which literally sent Triple H running. He couldn’t escape, and an already bloodied champion caught Barbie right between the eyes. Triple H tried to escape harm by climbing the cell, but Cactus Jack went after him.

As Jack reached the top, he placed Barbie on top only for Triple H to stomp at his hands and send Cactus Jack plummeting off the cell and through a table at ringside. Somehow, he continued to fight back and reached the top of the cell, where the brawl even saw Barbie get lit on fire. Some more back and forth led to a back body drop that was the beginning of the end, as Cactus Jack crashed through the top of the cell and through the ring below.

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Triple H carefully made his way back inside the cell, only to be shocked by the fact that Cactus Jack was still moving. He was laying in a hole in the ring, but he wasn’t done yet. Cactus Jack crawled out, refusing to quit before a few strikes and one final Pedigree sealed the deal. Triple H took the win, Cactus Jack’s career was “over” (as far as we knew at the time), and Hell in a Cell had been forever changed. I doubt we’ll ever see one quite like this again.

Final Ranking for all Hell in a Cell Matches

  1. Triple H vs. Cactus Jack at No Way out 2000
  2. The Undertaker vs. Edge at SummerSlam 2008
  3. The Undertaker vs. Shawn Michaels at Badd Blood: IYH in 1997
  4. The Undertaker vs. Mankind at King of the Ring 1998
  5. The Undertaker vs. Brock Lesnar at No Mercy 2002
  6. Triple H vs. Batista at Vengeance 2005
  7. The New Day vs. The Usos at Hell in a Cell 2017
  8. Triple H vs. Shawn Michaels at Bad Blood 2004
  9. Triple H vs. Chris Jericho at Judgment Day 2002
  10. The Undertaker vs. Triple H at WrestleMania 28 in 2012
  11. John Cena vs. CM Punk vs. Alberto Del Rio at Hell in a Cell 2011
  12. Kurt Angle vs. The Undertaker vs. Triple H vs. Steve Austin vs. Rikishi vs. The Rock at Armageddon 2000
  13. The Undertaker vs. Randy Orton at Armageddon 2005
  14. Sasha Banks vs. Charlotte Flair at Hell in a Cell 2016
  15. Roman Reigns vs. Bray Wyatt at Hell in a Cell 2015
  16. Seth Rollins vs. Kevin Owens at Hell in a Cell 2016
  17. Seth Rollins vs. Dean Ambrose at Hell in a Cell 2014
  18. Randy Orton vs. Jeff Hardy at Hell in a Cell 2018
  19. Kevin Owens vs. Shane McMahon at Hell in a Cell 2017
  20. D-Generation X vs. Legacy at Hell in a Cell 2009
  21. Triple H vs. Kevin Nash at Bad Blood 2003
  22. The Undertaker vs. Brock Lesnar at Hell in a Cell 2015
  23. D-Generation X vs. Mr. McMahon, Shane McMahon, and Big Show at Unforgiven 2006
  24. Randy Orton vs. Daniel Bryan at Hell in a Cell 2013
  25. Randy Orton vs. John Cena at Hell in a Cell 2014
  26. Randy Orton vs. Sheamus at Hell in a Cell 2010
  27. Roman Reigns vs. Rusev at Hell in a Cell 2016
  28. The Undertaker vs. Batista at Survivor Series 2007
  29. The Undertaker vs. Shane McMahon at WrestleMania 32 in 2016
  30. Roman Reigns vs. Braun Strowman at Hell in a Cell 2018
  31. Randy Orton vs. John Cena at Hell in a Cell 2009
  32. Randy Orton vs. Mark Henry at Hell in a Cell 2011
  33. The Undertaker vs. Kane at Hell in a Cell 2010
  34. Mankind vs. Kane at Raw is War in 1998
  35. The Undertaker vs. CM Punk at Hell in a Cell 2009
  36. The Undertaker & Steve Austin vs. Mankind & Kane at Raw is War in 1998
  37. CM Punk vs. Ryback & Paul Heyman at Hell in a Cell 2013
  38. CM Punk vs. Ryback at Hell in a Cell 2012
  39. John Cena vs. Alberto Del Rio vs. CM Punk vs. Dolph Ziggler vs. Jack Swagger in a dark match after Raw in 2011
  40. The Undertaker vs. Big Boss Man at WrestleMania 15 in 1999